


When the Assassin met the Mafia Boss

by sophie_cherie



Series: Not just a trophy wife [1]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Assassin Dean Winchester, Bottom Dean Winchester, Hurt/Comfort, Light Angst, M/M, Mafia AU, Mafia Boss Castiel, Panty Kink, Protective Dean Winchester, Rough Sex, Russian Mafia, Serial Killer Dean Winchester, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2019-07-15
Updated: 2019-07-16
Packaged: 2020-06-29 02:36:55
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 2,857
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19820803
Author URL: https://archiveofourown.org/users/sophie_cherie/pseuds/sophie_cherie
Summary: This is the prequel to my first story "Not just a trophy wife"The young Mafia Boss Castiel is in trouble. His brother Raphael wants him dead and he is gaining followers by the minute. To stop him from taking his place, Castiel hires an assassin, unknowing of just how important the killer will become to himself.





	1. Chapter 1

**Author's Note:**

> The prequel some of you asked for is finally here!!! Sorry for taking so long, I hope you will at least enjoy this.

"Castiel you have to do something, Raphael is getting stronger every day. He's convincing our men that you are too young to lead and shouldn't have been named Pakhan."  
Gabriel paced up and down in front of his little brother, getting more and more annoyed with him for not showing any reaction to his report.

"Does Raphael suspect you of being a double spy?" - Castiel asked calmly.

"Not yet, but I don't know how much longer I can keep up the facade," - Gabriel turned around to look at Cas - "which is why you shouldn't wait much longer to fight back. I know you're smarter and stronger than any of our brothers, so I don't get why you refuse to react to Raphael's provocations!" 

"I'm sorry for putting you in such a position Gabriel, but I needed time. I can't be caught killing my own brother and he's too well protected for just any assassin. Lucky for us I know Bobby Singer." 

"The old adviser of John Winchester? What's he got to do with anything? I thought he retired after the massacre of his Clan." - Gabriel asked. 

" Well yes, but he is the only person who can get in contact with David Yaeger, the only person aside from perhaps myself who is able to take out our dear brother and his lackeys. He was after all the one who took out the Winchester Mafia, all in one night." - Castiel smirked, knowing, that Raphael was as good as dead. 

Upon hearing this, a wide-eyed Gabriel had to sit down. "You actually got the Hunter? But he's a legend, a ghost!"

"A ghost that I'm gonna meet in"- Castiel looked at the big clock hanging above the door in his office- " about three hours, so I have to leave now. We're meeting in the Lebanon safe house. If I don't call by 3am, I want you to burn any evidence that you ever worked with me. I won't have you killed too."  
Seeing Gabriel's unhappy expression he added: "I know you don't like it, I hate the thought of it as well, but Raphael will probably take over after me, so you will have to accept him if you want to survive." 

Getting up, Castiel put a hand on his brother's shoulder and gave him a reassuring squeeze before leaving.

At 11pm sharp, Dean knocked on the door, surprised by the lack of guards on his way up the path to the hidden house. Usually his clients had at least half a dozen guards with them, even though they wouldn't be able to help them anyways. If Dean wanted someone dead, they were dead, no matter what protections they had.  
"Maybe they are in the house", he thought to himself as the door opened to reveal a handsome man with the bluest eyes he had ever seen.  
Dean guessed he was around thirty, the same age as himself. Quickly assessing his opponent and seeing the obviously tailored Armani suit and his dominant demeanor, he gathered that the man must be Castiel Krushnic, the russian Mafia Boss who contacted Bobby about him. Luckily for himself, he had almost perfect control over his facial expression, otherwise he wouldn't have been able to hide just how hot he found his client.  
However, he still couldn't help the little smirk playing around his lips as he saw Castiel's eyes widen in surprise because of Dean's casual outfit of plaid and jeans.  
Dean's reaction seemed to pull the man out of his stupor and he beckoned him inside and asked for his drinking preferance. 

Wanting to test the Mob Boss, who somehow managed to pique his curiosity in the few seconds they knew each other, Dean, instead of answering, walked further into the room, looked around a bit and finally turned to watch Castiel.  
Using his knowledge of the on-goings of the Russian Bratva -thanks to his own spying skills he knew the basics of what was going on in every Mafia- he playfully asked. "How do you know I wasn't already hired by Raphael to kill you?"

"Are you?", Castiel inquired, not showing any sign of being nervous.

"Maybe", Dean replied, walking closer while not breaking eye contact. 

Only standing a foot apart, they looked at each other calculatingly before suddenly drawing their weapons, Castiel an elegant silver blade and Dean a rustic knife.  
Quick as a snake Dean went for Cas's throat, not expecting there to be much of a fight, seeing as he hadn't ever met anyone who could keep up with him.  
His opponent however had other ideas and easily sidestepped Dean, who in turn threw himself at Castiel yet again, this time managing to make him fall.  
Rolling around on the floor he taunted the Russian: "shouldn't have worn a suit".

Snarling, Castiel turned their positions so that he was on top of Dean and held the blade to his neck: "Why shouldn't I kill you?" 

"Because you'd lose your balls and we wouldn't want that now, would we?", Dean grinned, his teeth bloody from a split lip, holding his knife between their bodies.

Keeping completely still, the two of them looked into each other's eyes for what felt like half an eternity, the only sound their panting.  
Dean could feel himself harden under the intense stare and in turn saw Cas's pupils widen.  
Finally Castiel gave in and surged forward in a brutal kiss, tongues and teeth clashing in a passionate dance.  
Turning them, so that Dean was sitting in Castiel's lap, he ground his ass back onto the other man's hardening lenght as he pulled of his shirt and ripped open Cas's dress shirt, sending several buttons flying.  
Upon seeing Dean's perky nipples, Cas leaned forward and took one in his mouth, licking and biting enough to turn it cherry red. It drove Dean mad with want and he let out obscenely loud moans.  
Gripping Dean's hair, Castiel pulled him in another kiss and switched their positions once more, stripping Dean of his pants and revealing a pair of white lace panties, soaked through with precome.

"What do we have here? The pretty boy likes to wear panties.", Cas smirked.

Seeing the light blush spreading across Dean's chest, he continued: "I think I gotta take a closer look at that."  
Moving down his body, Castiel mouthed at the other man's cock through the panties.

"Turn over", he commanded Dean, who promptly complied.

Massaging his ass before pulling aside the lace to spread his cheeks, Cas rubbed a thumb over the fluttering hole in front of him and spit straight on it, making Dean pant with the filthiness of it.  
Pressing lightly, he stretched his other hand towards Dean's mouth: "Suck!".  
Satisfied once they were properly slick, Castiel replaced his thumb with the two wet fingers and roughly pressed them inside, immediatly going for Dean's prostate and relentlessly moving over it.  
Eventually his own cock demanded attention and he opened his slacks enough to remove the pressure.

"Condom, use a condom!", Dean panted against the floor.

Begrudgingly, Cas got up, went to the closest drawer -knowing that all his places were thoroughly stocked with condoms- and pulled one out alongside a small package of lube.  
Walking back, he saw Dean had shed all his clothes and was now practically presenting for him, moving his hips enticingly.

"What are you waiting for Pakhan?", he teased.

Growling at the improper use of his title, Cas knelt behind Dean, grabbed his hips to keep them still and gave his ass a hard slap: "Better show some respect, Yaeger!".

Momentarily distracted by the use of his pseudonym, Dean couldn't come up with a witty reply.

In the few seconds it took Dean to process the reminder that he was sleeping with a client right now, Cas had already ripped open the condom and was now spreading lube on his rock hard cock.  
Gripping his hips tightly, Castiel lined up and thrust in with one fluid motion.  
Still on edge from their earlier fight, he didn't pause for Dean to adjust. Instead he set a hard, almost punishing pace that made Dean arch his back in pleasure as his prostate was hit over and over again.  
The slaps of skin against skin could be heard all through the house.  
With his left hand, Cas seized hold of Dean's hair once more to pull him flush against his own body. His other hand reached around to stroke Dean's cock in time with his thrusts.  
After only a few minutes he could feel Dean's hole squeeze around his dick in a hard orgasm that took Cas over the edge as well.

Seeing Cas basically collaps next to him on the floor, Dean turned around and looked at him: "Damn Krushnic, didn't think you had it in you."

"You ready to talk business now, Yaeger, or do you still want to kill me?" Castiel asked exasperated.

"Nah, I just wanted to find out who you are."

Hearing this statement, Cas couldn't help but comment disdainfully: "So you sleep with every client?"

"What? No, I meant the fighting asshole!", Dean replied angrily.

"So I'm special then?"

"Didn't say that", Dean smirked even though he could feel a blush spreading across his body.

Getting up and giving Dean a hand to pull himself up, Cas asked: "Whiskey or Beer?"

"After this? Whiskey."

Bringing two glasses of scottish whiskey with him, he sat down on the dining table across from a now dressed Dean, unbothered by the fact that his own dress shirt was still hanging open and exposing his from sweat glistening chest to Dean's eyes.  
Giving Dean one of the glasses, he took a long sip of his own and reached for a prepared file about Raphael and his followers, explaining an attentive Dean all inner structures of his enemy.

About an hour later, they found themselves back at the door.

"I'll trust you will take care of it in due time, Yaeger?"

"Of course, I'm not some amateur!", Dean replied, insulted by the lack of trust in his abilities.

"Didn't say you were. Payment after you finished the job.", Cas said calmly.

Soothed by Cas's relaxed tone, Dean answered cheekily: "Sure thing, Pakhan", knowing exactly that it would rile the other man up.

Reacting just as Dean had predicted, Cas growled and pushed him against the door frame, one hand on his throat, leaning in to kiss him hard.  
Giving as good as he got, Dean bit down on Cas's lip before finally pulling back and leaving, only stopping to throw a quick wink over his shoulder at Cas, who was watching him walk away until he vanished in the darkness.


	2. Chapter 2

A week later they met again at Castiel's safe house, Raphael and his followers, a good third of the Krushnic Mafia, long dead.

"Hey there, Cas", Dean greeted smugly.

Nodding, Castiel beckoned him inside: "Yaeger".

Sitting down at the dining table, drinking beer this time, Dean explained how he'd done the job:   
"...and then when every guard was laid down at his feet either dying or already dead, Raphael actually tried bargaining with me, saying stuff like 'if you leave now I'll let you live' " -Dean laughed- "as if he'd stand a chance against me! I even gave him a knife to make it a bit more interesting, but he was so slow, it was almost boring slitting his throat." 

Cas chuckled, glad it had been such an easy job for the other man.  
"Guess I have to pay up now", he said, reaching for a black suitcase. "Money's in there, you can count it if you want."

Looking at him calculatingly, Dean slowly shook his head: "I trust you."   
Grinning he added: "If not, you know what will happen"

"Oh but darling remember, I can keep up with you", Cas winked, making Dean smirk as well at the memory.

"Getting up Dean said: "pleasure doing business with you Krushnic", a hint of sadness at the prospect at saying goodbye glimmering in his eyes as he opened the door.

"The pleasure was all mine", Cas answered, pulling a surprised Dean in an open mouthed kiss.

Quickly catching himself, Dean kissed back just as ferociously before suddenly turning away and looking out into the darkness.

"Wha-", Cas began, interrupted by Dean's finger on his lips.

Listening intently for any noises, Dean's eyes marginally widened as he grabbed Castiel's hand.  
"Run!", he yelled, hauling a startled Cas with him down the path away from the house.  
Seconds later they heard a loud boom as the entire house lit up in a huge explosion, illuminating their surrounding, so that over a dozen men dressed all in black encircling them became visible, everyone of them carrying a variety of weapons.  
Pushing Castiel behind himself, Dean drew his own gun when the circle opened up to let a beautiful red haired woman in.

"Abaddon", Dean and Castiel said in unison.

"Aw how cute, they even talk at the same time." -Abaddon grinned wolfishly, making the men around her snort- "Hello boys."

Taking a step forward, Castiel growled: "What do you want? Did Crowley send you? I thought we had an agreement!"

"Well, Castiel, you see, that's the thing, I had my own agreement with Raphael. Joined powers to kill you and that slimy british bastard. But thanks to your little Hunter bitch, I'll have to do it myself.  
At least your friend Bobby Singer knew how to find you. Of course he didn't give up the information willingly, but luckily I can be very convincing...", Abaddon explained smugly.

Horrified, Dean shouted: "What did you do to him?!"

"Wouldn't you like to know." -she smiled cruelly- "You'll never find out now."  
Turning to her men she gave them the signal to kill her enemies and walked back behind the lines.

Not hesitating, Dean immediatly started shooting people while Cas pulled out two blades and went to the closest man, swiftly cutting his throat and going to the next person.   
Swirling around to look at Castiel, he saw him hacking his way through the rows, drenched from head to toe in sweat and blood, the sight glorious to Dean, who felt the first swirl of arousal simmering just beneath his skin.  
However, the milisecond distraction quickly became fatal as Abaddon used it to stab him in the back, deep enough for her blade to emerge from the other side.  
Ignoring the excrutiating pain, Dean acted as fast as he could, knowing he had only minutes before he'd pass out, pulled out his knife and beheaded her.

Castiel had meanwhile managed to kill the last of Abaddon's men and triumphantly moved to face Dean. Grinning ferally, he didn't notice the other man's injury until Dean broke down.   
All blood drained from his face and he ran forwards just in time to catch him.  
Pulling out his phone, he speed-dialed his brother: "Gabriel, I need a medical team at the safe house now! I don't have time to explain, just do what I say, Yaeger is hurt!".  
Hanging up, he looked at a barely conscious Dean.

"Dean, my name is Dean.", he whispered weakly.

"Dean, please stay with me", Castiel murmured softly.

Coughing up blood, Dean grinned: "Don't worry Cas, Winchesters are hard to kill."

Despite his eyes widening slightly with the knowledge that Dean must've killed his own family, Castiel chose to ignore this information for the moment and instead focused on putting pressure on the wound.  
Gabriel, who had luckily been close by, picked that moment to arrive with several doctors, all part of the Bratva, in tow.  
Carefully carrying Dean to one of the big trucks, they drove of towards the bunker, the Krushnic headquarter, just as another team of men arrived to extinguish the flames and take care of the bodies.

"Bobby", Dean awoke with a start.

"Dean, you are awake!", Castiel said from a chair at the side of the large double bed, taking the other man's hand.

"Cas?" -Dean asked confused- "What are you doing here? Where am I? I have to get to Bobby!"

"Shh, calm down, you are in our headquarter, just outside of Lebanon, it's not far away from the safe house we met in. My doctors treated you after Abaddon stabbed you. That was 2 days ago.  
Bobby is alright, or as alright as he'll ever be.", Cas explained regretfully. "He lost all feelings in his legs and has to use a wheelchair but he is alive. He is here actually if you want to see him."

"Oh thank God! ...Wait, you still didn't answer my first question, what are you doing here?", Dean asked suspiciously.

Blushing, Castiel stuttered: "I realize this is probably the wrong time..but..well....after all that happened, I was wondering if you would like to go out with me some time."

"Well, well, well, who would've thought Castiel Krushnic would be up for dating", Dean started to smile.

"That didn't answer my question", Castiel replied warily

"Of course idiot! C'mere"

Now smiling as well, Cas carefully leaned over Dean, mindful of his heavily bandaged torso, and kissed him softly.

**Notes for the Chapter:**

> Thanks for reading, I hope you liked it <3<3

**Author's Note:**

> I'll post the second chapter tomorrow:)


End file.
